Category: chiral-catalyst

Name is (S)-2-(Methoxymethyl)pyrrolidine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 63126-47-6, its synthesis route is as follows.,63126-47-6

To a mixture of lithium 7-chlorothieno [3,2-b] pyridine-2-carboxylate (6.59 g, 30 [MMOLE)] in DMF (100 [ML)] were added diisopropylethylamine, (6 [ML,] 4.45 g, 34.4 mmole), benzotriazol- 1-yloxytris (pyrrolidino) phosphonium [HEXAFLUOROPHOSPHATE] (16.16 g, 31 mmole) and [S- (+)-2-] (methoxymethyl) pyrrolidine (3.73 g, 32.4 [MMOLE).] The resultant reaction mixture was stirred at ambient temperaure for 16 hours. The crude reaction mixture was poured into water (600 [ML)] and extracted with EtOAc (3 x 200 ml). The combined organic extracts were washed with water (4 x 200 ml), dried over [NA2SO4] and concentrated, in vacuo, to give 8.8 g of an amber oil, which was purified by silica gel chromatography. Elution with Et2O : EtOAc (67: 33) and evaporation of the appropriate fractions gave 6.89 [G] (74percent) of an orange [SYRUP.APOS;H] NMR (DMSO-d6): 8 8.62 (1 H, d, J = 5.0 Hz), 7.88 (1 H, s), 7.35 (1 H, d, J = 5.0 Hz), 4.54-4. 47 [(1 H,] m), 3.93-3. 75 (2H, m), 3.71-3. 55 (2H, m), 3.37 (3H, s), 2.15-1. 92 (4H, [M). ANAL. CALCD.] for [C14H1SN202SCI] : [C,] 54.10 ; H, 4.87 ; N, 9.01 ; S, 10.32 ; Cl, 11.41. Found: C, 53.96

With the complex challenges of chemical substances, we look forward to future research findings about (S)-2-(Methoxymethyl)pyrrolidine

Reference£º
Patent; PFIZER INC.; WO2003/106462; (2003); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belong chiral-catalyst compound,trans-Cyclohexane-1,2-diamine,1121-22-8,Molecular formula: C6H14N2,mainly used in chemical industry, its synthesis route is as follows.,1121-22-8

Into a solution containing 1,6-diisocyanatohexane (4.03 grams, 24 mmol; obtained from Sigma-Aldrich Fine Chemicals) and a 1:1 mixture of hexane and tetrahydrofuran (100 milliliters) stirring at room temperature was added a solution containing triethylene glycol monomethacrylate (5.24 grams, 24 mmol; obtained as CD570 from Sartomer Company Inc., Exton, Pa.) dissolved in a 1:1 mixture of hexane and tetrahydrofuran (10 milliliters) and dibutyltin dilaurate (0.075 grams, 0.12 mmol (obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of 40 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for consumption of the triethylene glycol monomethacrylate reactant. The mixture was cooled to about 15 C. temperature, after which to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.37 grams, 12 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in a 1:1 mixture of hexane and tetrahydrofuran (10 milliliters). The reaction mixture was stirred for 1 hour while warming up to room temperature. FTIR spectroscopic analysis of a reaction sample showed little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Any residual isocyanate reagent was quenched by addition of methanol (5 milliliters). The reaction mixture was then filtered by vacuum filtration to give 6.13 grams of a solid product as a white powder (58 percent yield). 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 MHz) at room temperature (25 C.) and exhibited spectral assignments that matched those found for the compound in Example XVIII. The product was believed to be of the formulae

With the synthetic route has been constantly updated, we look forward to future research findings about trans-Cyclohexane-1,2-diamine,belong chiral-catalyst compound

Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is N,N’-Bis(salicylidene)-1,2-propanediamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 94-91-7, its synthesis route is as follows.,94-91-7

General procedure: To a round-bottomed flask with a stir bar was placed with [Ru(PPh3)3Cl2] (868 mg, 2.0 mmol) under the nitrogen. Pre-dried THF(10 mL) was added and the resulting mixture was stirred at room temperature. Then salen-enH2 (536 mg, 2.0 mmol) and a little excess of Et3N (252 mg, 2.5 mmol) in THF (5 mL) were added. The reaction mixture was stirred at room temperature overnight. After removal of solvents, CH2Cl2 (15 mL) was added and the solution was filtered through cilite. The filtrate was concentrated and the residue was washed with Et2O (5mL 2) and hexane (5 mL 2) to give the desired product. Recrystallization from CH2Cl2/Et2O (1:2) afforded green block-shaped crystals of [RuCl(PPh3)(salen)] (3) suitable for X-ray diffraction in three days. Yield: 1011 mg, 76% (based on Ru).

With the complex challenges of chemical substances, we look forward to future research findings about N,N’-Bis(salicylidene)-1,2-propanediamine

Reference£º
Article; Tang, Li-Hua; Wu, Fule; Lin, Hui; Jia, Ai-Quan; Zhang, Qian-Feng; Inorganica Chimica Acta; vol. 477; (2018); p. 212 – 218;,
Chiral Catalysts
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(S)-(1-Ethylpyrrolidin-2-yl)methanamine, cas is 22795-99-9, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,22795-99-9

In a 100 mL eggplant bottle, 1.22 g of benzaldehyde, 30 mL of anhydrous ethanol,(S) -1-ethyl-2-aminomethyltetrahydropyrroline, and the mixture was heated under reflux for 24 hours. Adding 0.76 g of sodium borohydride, stirring for 3 hours, pouring into water, extracting the organic phase with dichloromethane,Dried over anhydrous magnesium sulfate, and the solvent was removed to obtain a pale yellow viscous liquid.30 mL of absolute ethanol, 0.6 g of paraformaldehyde, 1.63 g of 2,4-dichlorophenol were added, and the mixture was heated under reflux for 12 hours.The crude product was chromatographed on silica gel to give red liquid L1 (2.32 g, 59.0percent).

22795-99-9 is used more and more widely, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine

Reference£º
Patent; East China University of Science and Technology; Ma, HaiYan; Wang, haobing; (35 pag.)CN103787943; (2016); B;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is 1,3-Dimesityl-1H-imidazol-3-ium chloride, and cas is 141556-45-8, its synthesis route is as follows.,141556-45-8

taken the imidazole chlorine salt [(R 1 NCHCHNR 1) CH]Cl (0.34 g, 1.0 mmol), ferrous bromide (0.22 g, 1.0 mmol) and sodium bromide (0.33 g, 3.2 mmol), in thf as the solvent, the 60 C reaction under 16 hours. Centrifugal, supernatant fluid transfer, remove precipitation, is added to the supernatant liquid of the three ring hexyl phosphine (0.28 g, 1.0 mmol), in 30 C reaction under 6 hours. Vacuum to remove the solvent, hexane washing, drying, in a mixed solvent of toluene and tetrahydrofuran extraction, centrifugal supernatant fluid transfer, after concentrating the serum to obtain a target product, yield 84%.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimesityl-1H-imidazol-3-ium chloride

Reference£º
Patent; Suzhou University; sun, hongmei; li, zhuang; liu, ling; chen, qi; (17 pag.)CN105541922; (2016); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 22795-99-9, its synthesis route is as follows.,22795-99-9

Example 45 Synthesis of ({4-cycloheptylamino-6-[((S)-1-ethyl-pyrrolidin-2-ylmethyl)-amino]-1,3,5-triazin-2-yl}-phenyl-amino)-acetonitrile (143) To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20¡ã C. was added N-phenyl glycinonitrile (0.264 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cycloheptylamine (0.25 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at rt. Then, S-(-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography eluding with 96:3:1 methylene chloride:methanol:conc. ammonium hydroxide to yield 143, (0.300 g, 33percent) mp 53-55¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 6.9 min, 94.1percent purity; MS (ESI): m/z 449 (M+H, 100), 381 (1.2), 353 (16.2), 226 (19.9), 225 (54.3), 212 (20.5), 177 (18.3), 164 (9.6).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
Chiral Catalysts
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D-Phenylalanine, cas is 673-06-3, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,673-06-3

A mixture of 44 mL of conc. HNO3 and 34.6 mL of conc. H2SO4 was added dropwise to a solution of 50 g (0.303 mol) of L(D)-phenylalanine in 150 mL of 85% H2SO4, pre-cooled to 10C. The reaction mixture was stirred for 3 hours at 8-10C, then the reaction mixture was adjusted to pH 6 by addition of NaOH aqueous solution. The precipitate was filtered off and dried. The reaction product was recrystallized from water. Yield 91% (2), 89% (2b). mp 240C (mp 239-241C [10]). IR spectrum nu, cm-1: 3294, 2889, 1701, 1620, 1535, 1443, 1350, 880, 864, 745, 698, 525. 1 NMR spectrum (DMSO-d6), delta, ppm: 2.90-4.00 m (5H, CH, CH2, NH2), 7.55 d (2Harom, 3J 8.5 Hz), 8.15 d (2Harom, 3J 8.5 Hz). 13 NMR spectrum (DMSO-d6), delta, ppm: 40.79 (2), 57.28 (), 128.15, 129.79, 145.41, 168.48 (arom), 172.84 (). Mass spectrum (ESI), m/z: 211.0713 [M + H]+. C9H10N2O4. Calculated M210.0641.

With the rapid development of chemical substances, we look forward to future research findings about D-Phenylalanine

Reference£º
Article; Tolstyakov; Tolstobrova; Zarubina; Popova; Protas; Chuprun; Trifonov; Russian Journal of Organic Chemistry; vol. 52; 11; (2016); p. 1681 – 1685; Zh. Org. Khim.; vol. 52; 11; (2016); p. 1686 – 1690,5;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is trans-Cyclohexane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 1121-22-8, its synthesis route is as follows.,1121-22-8

To a solution containing 1,6-diisocyanatohexane (5.04 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals, Milwaukee, Wis.) and anhydrous tetrahydrofuran (100 milliliters) stirring at room temperature was added 1,4-butanediol vinyl ether (3.48 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals) and dibutyltin dilaurate (0.19 grams, 0.3 mmol; obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of about 65 C. for 25 minutes. The progress of the reaction was monitored by 1H-NMR spectroscopy for consumption of the 1,4-butanediol vinyl ether reactant, indicated by the disappearance of the -CH2OH multiplet, which appears at 3.5 ppm as a shoulder peak on the downfield end of the intermediate isocyanate product whose signal is located at 3.35-3.40 ppm. The mixture was cooled to about 15 C. internal temperature after which to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.71 grams, 15 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in anhydrous tetrahydrofuran (10 milliliters). The mixture was stirred for about 60 minutes while warming up to room temperature, and thickened to form a gelatinous slurry. FTIR spectroscopic analysis of a reaction sample showed little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Any residual isocyanate was quenched by addition of methanol (5 milliliters). The reaction mixture was then filtered by vacuum filtration to give a semi-solid product, which was subsequently stirred in hexane to ensure full precipitation. The solid product was filtered and dried in air to give 8.17 grams of a white powder (79 percent yield). The product was believed to be of the formulae 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 mHz) at high temperature (60 C.) and indicated the above structure with the following assigned peaks: 1.05-1.90 ppm (several multiplets, 16 H integration, 4 methylene protons from 1,4-butanediol vinyl ether portion, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 2.95 ppm (multiplet, 4 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O-); 3.2 ppm (broad singlet, 1 H integration, tertiary methane proton adjacent to urea group on cyclohexane ring); 3.70 ppm (multiplet, 2 H integration, NH(CO)O(CH2)4-O-C(Hc)C(Ha)(Hb)); 3.96 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 3.98 ppm (multiplet, 2 H integration, NH(CO)OCH2CH2CH2CH2-O-C(Hc)C(Ha)(Hb)); 4.20 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 5.60 ppm and 5.72 ppm (broad singlets, each 1 H integration, urea NH protons); 6.48 ppm (doublet of doublets, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 6.82 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for C: 59.80%, H: 9.15%, N: 12.31%; found for C: 59.36%, H: 9.53%, N: 12.58%.

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

[1,1′-Binaphthalene]-2,2′-diol, cas is 602-09-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,602-09-5

A solution of 5.73 g (20 mmol) of (1,1′-binaphthyl) -2,2′-diol and 4.10 g (20 mmol) of p-TsOH were dissolved in 150 mL of toluene,The solution was stirred at 100 & lt; 0 & gt; C for 12 hours.The reaction solution was cooled to room temperature,Adding a potassium carbonate solution thereto,The organic layer was extracted three times by using 60 mL of ethyl acetate.The organic layer thus collected was dried with magnesium sulfate,The residue obtained after the solvent was evaporated from the silica gel column chromatography was used to separate and purify the residue,To obtain 3.76 g of intermediate I-1 (yield: 70%).The compounds thus produced were determined by using liquid chromatography-mass spectrometry (LC-MS).

With the rapid development of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol

Reference£º
Patent; Sanxing Display Co., Ltd.; Shen Wenji; Li Yinyong; Jin Rongguo; Po Junhe; Li Xiaorong; Zheng Enzai; Huang Xihuan; Jin Meigeng; Liang Chengjue; (89 pag.)CN106565689; (2017); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is Benzo-18-crown 6-Ether, and cas is 14098-24-9, its synthesis route is as follows.,14098-24-9

General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.

With the complex challenges of chemical substances, we look forward to future research findings about 14098-24-9,belong chiral-catalyst compound

Reference£º
Article; Zielinski, Matthew E.; Tracy, Adam F.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1701 – 1704;,
Chiral Catalysts
Chiral catalysts – SlideShare